Title of article
Synthesis of (1S)-1-amino-2,2-dimethylcyclopropane-1-carboxylic acid via PLE mediated hydrolysis of bis(2,2,2-trifluoroethyl) 2,2-dimethylcyclopropane-1,1-dicarboxylate
Author/Authors
Antonio Salgado، نويسنده , , Tom Huybrechts، نويسنده , , Annelies Eeckhaut، نويسنده , , Johan Van der Eycken، نويسنده , , Zsolt Szakonyi، نويسنده , , Ferenc Fulop، نويسنده , , Alexey Tkachev، نويسنده , , Norbert De Kimpe، نويسنده ,
Issue Information
هفته نامه با شماره پیاپی سال 2001
Pages
6
From page
2781
To page
2786
Abstract
Hydrolysis of bis(2,2,2-trifluoroethyl) 2,2-dimethylcyclopropane-1,1-dicarboxylate with pig liver esterase afforded (1R)-2,2-dimethyl-1-(2,2,2-trifluoroethoxycarbonyl)-cyclopropane-1-carboxylic acid in high enantiomeric excess. This compound was rearranged to (1S)-2,2,2-trifluoroethyl-2,2-dimethyl-1-[(N-ethoxycarbonyl)amino]-cyclopropane-1-carboxylate via a Curtius type reaction with DPPA. Final alkaline hydrolysis gave (1S)-1-amino-2,2-dimethylcyclopropane-1-carboxylic acid.
Keywords
1-aminocyclopropane-1-carboxylic acid , Enzymatic hydrolysis , Curtius rearrangement , 2 , 2-dimethylACC
Journal title
Tetrahedron
Serial Year
2001
Journal title
Tetrahedron
Record number
1081859
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